HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Triethylamine → tert-butyl 2-{[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]carbonyl}hydrazinecarboxylate
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Triethylamine | HCID 8471 | — |
| Edukt | tert-Butyl carbazate | HCID 70091 | — |
| Edukt | Diethylphosphorylcyanide | HCID 13586794 | — |
| Edukt | 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzoic acid | HCID 57931763 | — |
| Lösungsmittel | Water | HCID 962 | — |
| Lösungsmittel | Dimethylformamide | HCID 6228 | — |
| Produkt | tert-butyl 2-{[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl]carbonyl}hydrazinecarboxylate | HCID 66608673 | 44,3% |
Reaktionsschritte
To a mixture of 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzoic acid (12.1 g) and tert-butyl hydrazinecarboxylate (7.61 g) in DMF (100 mL) was added diethyl phosphoryl cyanide (8.55 mL) at room temperature. After stirring at room temperature for 30 min, triethylamine (21.6 mL) was added, and the mixture was stirred overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (8.00 g).
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08822699B2 |
| Quelldatensatz | uspto-grants-2014_09 |
| ORD ID | ord-3792cda2947945bb985eb21bbdc96d17 |
| Quellennotiz | uspto-grants-2014_09 |